Quantum computing may not be breaking your security today, but the decisions you make now could determine how exposed your organization is when it does. Conor Deegan explains why CTOs need to start preparing before Q Day arrives.

Build your own CTO Playbook at www.theCTOplaybook.com, the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.

My guest this week is Conor Deegan, a security engineer, cryptographer, and co-founder of Project 11, focused on helping organizations prepare for the transition from classical cryptography to post-quantum cryptography.

The quantum threat goes far beyond Bitcoin and digital assets. Conor explains how quantum computing could eventually affect the cryptography behind banking, communications, cloud infrastructure, authentication, health records, and everyday internet security.

He breaks down what "Q Day" means, why organizations cannot simply wait until a powerful quantum computer exists, and how "harvest now, decrypt later" could put sensitive information collected today at risk in the future.

The transition also comes with real engineering challenges. Post-quantum cryptography can require more computing resources, memory, storage, and bandwidth, while legacy systems and constrained devices such as IoT hardware can make migration even more difficult.

Conor then shares a practical framework for CTOs: understand the threat, put someone in charge, identify critical systems and data, take the easy wins, put pressure on vendors, and stop creating migration debt.

You'll Learn:

[0:25] The Quantum Threat and Why It Matters

[3:54] Understanding Q Day

[7:52] How Quantum Computing Impacts Security

[11:22] The Mission Behind Project 11

[18:58] Harvest Now, Decrypt Later

[21:30] The Challenges of Post-Quantum Cryptography

[27:29] From Engineer to CTO

[30:20] A Practical Quantum Security Plan for CTOs

[36:56] Identifying Critical Systems and Data

[41:03] Taking the Easy Wins

[43:12] Preparing Vendors for the Quantum Transition

[43:57] Avoiding Migration Debt

[45:59] Building Crypto Agility

[48:35] The Quantum Challenge for IoT

[54:50] Preparing for Q Day

Find more from Conor Deegan and learn more about Project 11 through his professional channels: projecteleven.com, X, and LinkedIn. Conor welcomes direct contact on post-quantum migration questions.

Find more from Adam on https://www.linkedin.com/in/adamhorner/ and https://www.youtube.com/@TheCTOplaybook, and explore coaching, cohorts, and how you can stay up to date at the https://www.thectoplaybook.com/, helping you build your own playbook for your path at your pace.

If you prefer listening, check out the podcast at https://bit.ly/thectoplaybook.

Most CTOs think adopting AI means picking the right tools, but Sumeet argues the real work is closing the accountability gap between agents and engineers.

Build your own CTO Playbook at www.theCTOplaybook.com - the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.

My guest this week is Sumeet Vaidya, co-founder and CEO of Crafting, who spent years at Facebook, Uber, and Discord before building the infrastructure enterprise engineering teams now use to put agents to work safely.

His perspective matters because he sees what CTOs say publicly, and what their teams are actually doing internally, and the gap is bigger than most leaders want to admit.

Roughly 80% of enterprise engineering orgs, he estimates, are doing close to nothing meaningful with AI. The rest are either reacting to hype or trying to build something durable, and the difference is not the tools they pick.

One partner running 3,000 agents against 250 engineers changed how he thinks about capacity entirely. That number is where his six diagnostic questions come from and where the cracks appear first: brittle CI/CD, accountability gaps for agents, and a hiring pattern that's storing up debt for the next downturn.

If you're under pressure to show AI gains while cutting token spend, this one is aimed at you.

You'll Learn:

[0:00] Introduction

[2:25] The disconnect between what companies say and what teams do

[4:38] Why 80% of enterprises watch and wait on agents

[9:31] Chasing the latest model as a vanity metric

[14:14] Resilient cultures survive shocks that short-term thinking cannot

[15:46] The engineering cultures that shaped Sumeet's career

[28:51] Silicon Valley is not the whole world

[33:02] What breaks if you 10X the team today

[42:31] Hiring only senior engineers stores up hidden debt

[47:11] Turning engineers from code writers into builders

Find more from Sumeet Vaidya on LinkedIn, X, or explore the Crafting Website.

Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.